Polymer/HIO4 : An efficient catalyst for solvent-free synthesis of 2-naphthol azo dyes

Document Type: Articles


1 Departement of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, I.R. Iran.

2 School of Chemistry, Damghan University, Damghan, I.R. Iran.


A convenient, one-pot method for the synthesis of diazonium salt has been developed by the sequential diazotization of aromatic amines with NaNO2, polymer- supported periodic acid (PPIA) and 2-naphthole under solvent-free conditions at room temperature. By using this method, several types of aromatic amine, containing electron-withdrawing and electron-donating groups, were rapidly converted to the corresponding azo dyes in good to excellent yields. The ensuing aryl diazonium salts supported on polymer (aryl diazonium polymer), ArN2 +IO4 - were sufficiently stable to be kept at room temperature in the dry state. The use of mild reaction conditions and an inexpensive procedure are further advantages of this method.


[1] H. Zollinger, Color chemistry, synthesis, properties and application of organic dyes and pigments, 3rd Ed., Wiley VCH: Weinheim, 2003.
[2] P. Gregory, High-technology applications of organic colorants, Plenum press, New York, 1991.
[3] G. Viscardi, P. Quagliotto, C. Barolo, G. Caputo, G. Digilio, I. Degani, E. Barni, Dyes Pigments 57 (2003) 87-95.
[4] A. Fraleoni-Morgera, C. Della-Casa, P. Costa-Bizzarri, M. Lanzi, A. Missiroli, Macromolecules 38 (2005) 3170-3175.
[5] A.A. Jarrahpour, M. Motamedifar, K. Pakshir, N. Hadi, M. Zarei, Molecules 9 (2004) 815-824.
[6] M. Tonelli, I. Vazzana, B. Tasso, V. Boido, F. Sparatore, M. Fermeglia, M. S. Paneni, P. Posocco, S. Pricl, P. Colla, C. Ibba, B. Secci,  G. Collu, R. Loddo, Bioorg. Med. Chem. 17 (2009) 4425-4440.
[7] L.S. Goodman, A.Gilman, The Pharmacological Basis of Therapeutics, Mc Millian New York, 1970.
[8] L.R. Al-rubaie, R.L. Mhessn, E. J. Chem. 9 (2012) 465-470.
[9] A. Bamoniri, A,R. Pourali, S.M.R. Nazifi, Iran. J. Catal. 2 (2012) 185-189.
[10] A. Chakraborty, P.K. Saha,  C. Datta, 7th International Conference–TEXSCI, 6-8 Sept, Liberec, Czech Republic, 2010.
[11] T. Okuzumi, E. Nakanishi, T. Tsuji, S. Makino, Tetrahedron Lett. 44 (2003) 5539-5542.
[12] A. Vogel, Textbook of Practical Organic Chemistry Including Qualitative Organic Analysis (VOGELE’S), New York: Longman, 1978.
[13]    M.E. Moon, Y. Choi, Y. Min Lee, V. Vajpayee, M. Trusova, V.D. Filimonov, C. Ki-Whan, Tetrahedron Lett. 51 (2010) 6769-6771.
[14] A. Zarei, A.R. Hajipour, L. Khazdooz, B.F. Mirjalili, A. Najafi, Dyes Pigments 81 (2009) 240-244.
[15] T. Okuharat, Chem. Rev. 102 (2002) 3641-3666.
[16] J.H. Clark, Chemistry of waste minimization, Chapman and Hall: London, UK, 1995.
[17] J. Ibtissem, M. Faouzi, H. Jean, G. Christian, Molecules 14 (2009) 528-539.
[18] C. M. Adharvana, K.Syamasundar, Catal. Commun. 6 (2004) 67-70.
[19] N. Bicak, H. Bulbul, Polym. Bull. 46 (2001) 139-145.
[20] A.R. Pourali, M. Tabaean, S.M.R. Nazifi, Chin. Chem. Lett. 23 (2012) 21-24.
[21] A.R. Pourali, M. Ghanei, Chin. J. Chem. 24 (2006) 1077-1079.
[22] B.F. Mirjalili, A. Bamoniri, A. Akbari, Curr. Chem. Lett. 1 (2012) 109-114.
[23] B.F. Mirjalili, A. Bamoniri, A. Akbari, Tetrahedron Lett. 49 (2008) 6454-6456.
[24] B.F. Mirjalili, A Bamoniri, L. Zamani, Lett. Org. Chem. 9 (2012) 338-343.
[25] B.F. Mirjalili, A.H. Bamoniri, L. Zamani, Sci. Iran. 19 (2012) 565-568.
[26] B.F. Mirjalilia, A. Bamoniri, A. Akbari, N. Taghavinia, J. Iran. Chem. Soc. 8 (2011) 129-134.
[27] A. Bamoniri, B.F. Mirjalili, A.A. Jafari, F. Abasaltian, Iran. J. Catal. 2 (2012) 73-76.
[28] B.F. Mirjalili, A. Bamoniri, A. Akbari, J. Iran. Chem. Soc. 8 (2011) 135-140.
[29] B.F. Mirjalili, A. Bamoniri, N. Mohaghegh, Curr. Chem. Lett. 2 (2013) 35-42.
[30] A. Bamoniri, B. F. Mirjalili, S. Nazemian, Curr. Chem. Lett. 2 (2013) 27-34.
[31] A. Bamoniri, B.F. Mirjalili, S. Nazemian, J. Nanostruct. 2 (2013) 433-439.
[32] Colour Index, The Society of Dyers and Colourists, 3rd Ed., Bradford, UK, 1971.